


Jaime the cherry boy

by Take_me_Harder



Category: None - Fandom
Genre: Age Difference, Anal Sex, Large Cock, M/M, Oral Sex, Size Difference, Underage Sex, femboy
Language: English
Status: In-Progress
Published: 2021-02-16
Updated: 2021-02-16
Packaged: 2021-03-18 13:00:35
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 4,822
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29490210
Author URL: https://archiveofourown.org/users/Take_me_Harder/pseuds/Take_me_Harder
Summary: A boy discovered his sexuality early. Falling for his coach, he decides to make the coach fall for him as well.
Comments: 1
Kudos: 7





	1. Jaime gets extra practice

**Author's Note:**

> Jaime  
> Age 12  
> Height 4’7”  
> Waist 23  
> Hips 34  
> Turn ons : big cock, gentle men, hard sex and analingus.  
> Turn offs : small cocks, rude men and scat  
> Likes: being held in strong arms, ice cream (strawberry), big dogs, sunbathing and sushi  
> Dislikes: corn, little boys, waking up early and effeminate men (boys he is okay with)

Jaime was always a girly little boy. He liked to be pretty and liked the attention it brought. He really liked it when men would tell him how cute he was.

The first time Jaime had sex was with his elementary swim coach. Nathan was a powerfully built man, though slender, his body was none then less masculine. The boy at age 6 developed a crush immediately.

Jaime tried hard to impress his coach, asking his parents for more private practices. Jaimes father Tyler (a slender large bottomed, small cocked twink of a man. He and Jaime were similar in this way.) rejoiced that his son wanted to be more athletic than he was and agreed. His mother, Vanessa ( a completely stacked knockout only married to Tyler for his money) loved the idea as well. She could see the large bulges of the muscular coaches and older boys all she wanted this way. She and Jaime were similar in this way.

After a few years, Jaime was confused and frustrated. He loved being wet and especially loved Nathan spending time close to him, but didn’t fully understand why his tiny cock stood erect at night when he though of Nathan. His mind would wander to images of the mans imposing bulge, and his tiny thing would grow as hard as stone.

He would think of the thing between Nathan’s legs as flopping out down his thighs, and Jaimes tiny butthole would twitch and quiver. Thinking that there must be something inside of him that need to be reached, Jaime started to put his tiny fingers into his freshly cleaned tight pink hole. The first time for him was amazing.

He managed 2 fingers stretching out his perfect hole. Almost immediately he squealed with a dry orgasm. Jaime just knew something bigger would be even better. So he hatched a plan.

The next day, Jaime told his parents that he needed more practice for an upcoming competition. “Coach is depending on me, I’m the only one that can swim fast enough. He needs me to stay late tonight. I can get a ride home from him if it’s a problem.” His parents didn’t even question it.

So Jaime laid the trap. He would do everything he could to tempt coach Nathan. He thought about it all day. His little dicklett would have been more obvious if it was even a tiny bit bigger.

After school, the excruciatingly horny 9yo went to practice. He ignored the feeling of his bottom needing to be filled, he ignored his little cock wanting to get hard. He knew that his time would come.

After practice ended and finally all the other boys had left (he didn’t mind the older boys, some of them had bouncing packages much like the coach, a few seemed to even be bigger.), Jaime started his game. At first just demanding that Coach Nathan hold him while practicing his strokes.

In the water, the boy stopped and nestled up to the man, looking up with a coy expression. “I don’t know if I can perform as well as some of the other boys.” Nathan, trying to ignore the sexiness of the boys lips and face replied “you are so much better than them. I’ve put so much time into developing your body, you can take almost anything. No matter how hard it is.”

Nathan, upon hearing his voice and choice of words, became incredibly erect. Jaimes luscious ass was rubbing against him, there was no way the little boy didn’t feel his hot giant cock swelling up. “Jaime, I need you. You are the only one on this team that can move well enough for what I want... in this competition.” Nathan was nervous and so hard, the tip of his penis straining against his swimsuit, stretching the material to its limit.

Jaime felt the meat pressed against his back and giggles to himself. The little femboy takes his leave of the warm man, “I’m going to take a shower now. I always have trouble with my back, think you could help me?” Jaime asked.  
Nathans cock was rigid, luckily no one was around. “You get started, I will be in in a minute. We can talk about some exercises to get you ready for the meet afterwards.”

The boys ass jiggled as he walked towards the locker room. ‘That swim suit can’t be regulation, it’s basically a thong.’ Thought Nathan as his eyes were glued to the flawless bubblebutt and flared hips on Jaime. As the door closed, Nathan moaned and sighed with pent up lust. “You can’t be thinking of him like this, he doesn’t know he is teasing you.” Nathan said under his breath.

He waited a few minutes for his bulge to subside a bit and then focused on what he would have for dinner, just to distract himself. Nathan walked into the locker room and heard the shower going, steam was pouring out of the room. He disrobed and headed in.

Jaime was bent over and leaning against the wall, bracing with one hand while the other was 3 fingers deep in his bright pink hole. “Ooooo, coach daddy, that feels so good.” Jaime whispered. Nathans foot long cock stood to attention immediately, he shuddered as pre cum began to drip from the tip. “Jaime! What are you doing?!?” Nathan yelled. Jaime turned slowly, licking his pouty full lips, smiling with a hungry look in his eyes. “What do you mean Da... Coach? I’m just making sure I’m extra clean. This is why I wanted help, my widdle fingers just can’t get to all those hard to reach places.” He walked towards Nathan, grabbing the mans giant cock by the base. 

Jaime shook it and smacked it against his lips and cheeks. With a kiss to the tip, the slutty femboy wrapped his lips around the broad slick bulb. With a slurp and a pop, “this is exactly what I need... daddy.” Nathans jaw dropped as the heat of the boys mouth nearly made him melt. He couldn’t take anymore. 

“No one is here, fuck this you little slut!” Grabbing the back of the blonde boys head, he drove his cock into Jaimes eager mouth. “Gluk gluk gluk! shhhlurp! Mmmmmmm ‘Addy! Tosht sho gug.” Jaime spoke into the cock, taking it deeper and deeper.

Nathan liked being called daddy by the little femboy, he started to buck faster and faster, pushing the boy back against the wall. Looking down, he saw that Jaime was trying to keep his pretty eyes on Nathans face. The view was too much for the hung man. Jaimes lips felt the giant cock swell, and then his throat began to fill. The cock pulsed several times, pumping molten hot cum down the boys throat. The last two, Jaime pulled the cock out with a ‘Pop!’ and it coated his tongue and face.

“Daddy, I still need help... back here.” Jaime turned and wiggled his bouncy boy booty. Nathans cock was hard almost immediately. Jaime wiped some of the viscous cum from his face and worked it into his boy pussy. He grabbed the tip of Nathans cock and rubbed it against the tiny perfect hole. Jaime backed up, pushing the tip in with a gasp and a moan “uuuuggh, fuck, it’s so fat! Daddy, I love it!”

Unable to control himself any longer, Nathan grabbed the boys hips and thrusted. The hole was lubricated, it was clearly well used, and he pushed all the way to his base in one go. “AAAAAAHHHHYesyesyesyes! Ooooooooooo! Gimme that dick Dah-Deeeeee!” Jaime squealed. The man pulled dick out half way and thrusted it back in even harder. He pulled it back until only the tip was still in and then pushed it back to the base. He felt his Juicy fat balls smack the boys tiny testes. “You tight little slut! FUCK THIS PUSSY IS GOOD!” Nathan yelled.

The boys ass jiggled as it stretched and twerked back on the massive penis. Jaimes eyes glazed over, his plump cherry lips drooling like his boy clit. Every pump hitting his little p-spot and milking it just a bit more. “Oh daddy! Just like that! Harder daddy! Claim that little cunny DADDY! Oooooooooo” 

Nathan picked up his tiny partner, hooking his strong arms under the boys juicy thighs. He began to thrust up into the boys body. He looked down to see the little femboys tongue hanging over his juicy lips, drooling onto his slender tummy. Well, slender before it started to bulge from the big dicking. Nathan laughed. “DAH...Deee... I... wanna... be on... top.... uuuunnnnggghh!” The boy spoke through the pounding has he shot another tiny thin watery load.

The man walked over with Jaime still on his dick against his chest, over to a bench. He threw some towels down and then slowly pulled out from the boys pussy. It grasped and held on to his cock head, he finally managed to pull it from the greedy hole, Jaime squealed in pleasure. Nathan laid down on the bench.

Jaime mounted the man like a horse, leaning over and kissing the hung hunk “I’ve liked you for a long time, daddy. I want to look at you as we make love.” The boy slut said as he grabbed the giant cock once more. Sliding it in all the way to the base, Jaime shot another load onto Nathan’s chest. “You should make me yours daddy. We could do this everyday, even more if we are at a meet over night.” 

The boy writhed as the cock deep inside of him bulged out his tummy, twitching and swelling like it was about to blow. Jaime wrapped his arms around Nathan’s head and kissed him deeply, passionately and lovingly. He whispered into Nathan’s lips “mmmmmm, fill me up daddy. Fill my little cherry hole.”

Nathan couldn’t hold it any longer. His balls rose up, his fat cock swelled and his cum churned to the top. “You beautiful little cherry boy.... oh fuck.... take it all!” Grabbing Jaime by the hips and pulling him down all the way, squeezing any amount of dick not already in the boy up even farther, he came. Hard. “Ooo, Daddy! Yes! Yes! Yaaassss!” Jaime squealed. 

Rope after rope of hot, thick cream pumped into the boy. His tummy expanded a bit, almost looking pregnant, Jaime collapsed onto Nathans chest. After a few minutes, the long cock softened and plopped out of the tight but pliant hole. A surprising calm washed over nathans whole body.

“What were the exercisesyou wanted me to do? The ones to get me ready... for the Meat?” Jaime giggled.


	2. Love at home

**Summary for the Chapter:**

> Nathan want to get Jaime something special. He then figures out how to spend a little more time with his little boyfriend.

**Notes for the Chapter:**

> Mostly Nathan, but definitely picks up in the end.

A few months had assed since the first time that Jaime had manipulated Nathan into sex. After a couple of weeks of late “practices”, Nathan realized that he had been played. He didn’t mind though, Jaime still practiced with the other boys, his parents still thought a strong male influence was good for Jaime and the sex was mind blowing.

One day, Nathan thought that he would drop the pretense and hold “special practice” at his house. Jaime was excited, he wanted to feel that dick on a bed. To commemorate this special time, Nathan went to a specialty store to get Jaime a gift. Something just for the two of them.

After a bit of research, he found the place he was looking for, ‘Lovers secret’. It was a a nicer sex shop, with more upscale apparel and novelties. Nathan left work a little early and headed down.

As soon as he walked in, he felt a little nervous, but a pretty young woman with light blue hair pulled up into a bun walked over to him and asked “Hi, can I help you find something?” She smiled at him. Nathan felt reassured and responded “My girlfriend is a bit on the tiny side, a little under 5’. She is hard to shop for, do you have anything that might fit her?”. The girl whose name tag read ‘Amber’, looked him up and down, then smiled. 

“And you so... tall and strapping. I bet you two look so hot.” Amber said, biting her index knuckle, gazing down at Nathans noticeable bulge in his slacks. “We cater to all kinds here, so I think I can help!” Amber walked away, waving the muscular man to keep up with her. Ambers mind wandered to thinking about what the two of them looked like. “His cock couldn’t possible all fit in her, could it?” She said under her breath.

Nathan’s ears perked up “what did you say, I missed that.” Amber blushed and responded “I think this could fit her, couldn’t it?” And she grabbed a set of white lacy lingerie. The top looked a bit more like a lacy halter top than a bra, the tiny patch of fabric on the front of a g-string and a tiny waisted garter belt. “If you like this kind of look, I have stocking that go with this as well.” The outfit looked like something a bride would wear on her wedding night.

Nathan’s cock began to swell, his boxers unable to contain it, it slithered down his pant leg. “It looks perfect” he said. Amber, trying not to obviously look at his dick, sighed and said with a wry smile “I bet it does, big boy!”. Nathan blushed. They walked over and she gift wrapped it, he thanked her paid for it and walked to the door. “Come back any time, I would love to help you again. Bring your lady next time!”

She smiled as Nathan turned back to wave goodbye. After he left, she locked the door, but up the back in 10 sign and grabbed one of the footlong toys. She headed into her office and sucked on the tip, thinking about that man and his tiny bride. Her pussy was sopping wet, she knew this was going to be good.

——————————————————————

Nathan drove around picking up a few supplies, and then wrote an email to all but Jaimes parents. “Practice is canceled today. Something of a personal nature came up and needs to be handled immediately. Sorry for the inconvenience.”

He then wrote another email to Jaimes mother “I would like to pick up Jaime from school today for an early extra practice. After regular practice today I have a specialist coming in to massage him and make sure he is ready for the away meet next week. I would have him back around 830-9.” 

A few minutes later his phone dinged “that’s a great idea Nathan. Thank you for taking such an interest in my little boy! With you as his role model, I know he can take on anything. Make it 10 and you boys get something to eat, I will reimburse you for it. He doesn’t have school tomorrow anyway.” Jaimes mother replied. So he would have from 3-10pm with his little lover? 7 uninterrupted hours? His cock began to leak just thinking about it.

As he pulled into his driveway, his phone dinged again “Nathan, this is Tyler, Jaimes father. I have a bit of a favor to ask you. I’d like to whisk the wife away for a romantic weekend, would you mind looking after Jaime for the weekend? We would be back Sunday night, and I would be glad to pay you for your trouble. Jaime has a key, so you can drop by later to pick up clothing, or you could just sleep here. What do you say, care to help a guy out?”

Nathan couldn’t believe his luck, this man was willing to pay for him to have Jaime all to himself for the weekend. He replied “No trouble at all Tyler. You know the little guy is always welcome with me. Just give me the rate you would give a teenager to watch him for the night. I’m glad to do it anytime you go out of town.” A few minutes later, his phone dinged again.

“I’m going to hold you to that offer! We haven’t really had alone time since before Jaime was born. I love my son, but you could help my marriage out by watching him sometimes. Thanks again, I will Venmo you a few hundred for the weekend.”

Nathan ordered a couple of pizzas and a large salad for the night. They would be here around 7, plenty of time to have some fun, get cleaned up and look like a father and son watching movies. This was the best feeling he had ever had. Nathans stomach felt fluttery and his heart felt light, was he in love with Jaime?

Nathan pulled up to Jaimes school, his mother had give Nathans name to the office so he could pick him up. After a few minutes, Jaime walked out of the front door, he smiled at Nathan and said goodbye to his friends. He got in the car and fought his desire to kiss his lover.

Nathan also fought with his desire to break many road laws and not just recklessly speed the whole way home. “We have to stop by your place to get some clothes, but then it’s off to my house.” He smiled. Jaime put his hand on the mans crotch, “I could just not wear anything, I know you like that.” He said softly, gripping the stiffening cock. Jaime started to unzip Nathan’s pants.

“Not yet, cherry. You gotta wait for it. Soon, we just need to do this and then I’m all yours.” Nathan said with all his resolve. “Fine, your no fun.” Jaime huffed. They pulled up Jaimes driveway, the boy hopped out. A few minutes later, ha came out wearing just baggy swim shorts and a open short sleeve button up.

The took off and by 330, had arrived at Nathan’s house. As they entered the door, Nathan closed it with his heel, locked the door and swept Jaime in his arms like a bride. Jaime reached for Nathan’s handsome face and pulled it in for a deep kiss. Nathan walked Jaime upstairs in his arms, gently kicking open his bedroom door and placing Jaime on the bed.

With out delay, Jaime shimmied his shorts down his hips. He wasn’t wearing anything under them, his tiny pink cocklet sprang up. He scooted to the edge of the bed, the way he sat accentuated his girlish hips, narrows waist and fat bottom. He slowly unzipped Nathan’s pants letting them drop to the ground. Jaime nuzzled his face into the swelling bulge in Nathan’s boxers.

He rubbed his face all over, then pulled down the boxers. Nathan’s hard cock slapped Jaimes in the face. Placing one finger under the wet, glistening tip, he lifted it up to his pouty lips. Looking into his lovers eyes, Jaime licked his lips and sighed, the hot breath of the boy hitting the ever hardening penis. Jaime leaned down and kissed the tip, deeply, as he had kissed Nathan just moments ago.

Grabbing the giant dick with both hands, the boy clasped and started to squeeze and rub up and down. He kissed even deeper, his tongue started to play with the pre cum dripping slit. Jaime giggle “mmmmmmm, daddy, I love kissing you.” And with that, he opened his mouth wider, pushing his head down the shaft. “Gluk, gluk, gluk. Shhhluuurrrp-POP! Ooooo, daddy, you taste so good!”

Jaime was making love to Nathan with his mouth, and loving every bit of it. Nathan could feel what was coming, the first of many in fact, but he didn’t want it just yet. “Lay back cherry, spread your legs, I need to be in you.” With a slurp and a pop, Jaime giggled and did as he was told.

Nathan’s wet, dripping, throbbing cock pointed right at the perfect boy pussy. He pushed gently, the tiny hole giving little by little. With a short harder thrust, it snapped into the boys pussy. “Uuuuuuggghhnnnhhh” Jaime moaned, his tiny boy clit leaking with his first orgasm of the day. Nathan moved in and out easily, the tight hole lunricated by the slick and sloppy coating of spit and precum from Jaimes blowjob.

As he bottomed out inside the little femboy, Jaime wrapped his arms and legs around Nathan’s muscular torso. “ I LOVE YOU DADDY!” He yelled. “I LOVE YOU SO MUCH! DONT STOP! DONT EVER STOP!” He squealed, cumming once more. Nathan paused for a moment, looking into Jaimes beautiful green eyes, and kissed him.

In the impassioned kiss, Nathan sawed deeper and deeper into Jaime. Hard and deep, trying to push even deeper. “I love you too.” He whispered into Jaimes ear. Jaime seized up and came immediately from the pleasure, the depth and Nathan’s love.

Pulling his long, fat cock all the way to the flare of the tip, Nathan dove be back in harder and harder. After a few minutes of long, fast, hard sex Nathan knew he was going to come. He kissed the pretty boys plump lips once more, deeply with their tongues touching and swirling.

Jaime felt the tell tale sign of the fattening cock, his head flashed pure pink. His body felt like it was trying to melt as Nathan drove his glorious cock the farthest it’s ever been and unloaded. Jaimes legs unconsciously straightened and his toes curled, coming the hardest he ever has. The sheer torrent of Nathan’s cream flooded the boy immediately. 

It spilled out around the base of Nathan’s dick, with no more room inside. They held each other and kissed for a few minutes after that, neither wanting to let go yet. Nathan looked at the time, saw it was about 630. This marathon fuck session had finished just in time.

“Let’s get cleaned up, I ordered pizza, it will be here soon. After dinner, I have a gift for you.” He kissed the boy softly. “Because you are special” he kissed again. “Because you are sexy” he kissed again. “And most importantly, because I love you.” Jaime smiled and began to tear up. He had never been so happy.


	3. Yes I want pizza

**Summary for the Chapter:**

> Quick intro of a new character, then Jaime gets his present.

**Notes for the Chapter:**

> Sorry this one is so short, but I wanted it to be cute/sexy/loving.

The driver, Derrick, pulled up to Nathan’s house, he whistled when he saw it. This was a nice neighborhood and this was definitely one of the nicer houses. The large Black man stepped out of the vehicle, got the pizzas and the salad and walked to the door.

He had been working in this area for a while and while he did occasionally have scared old white people threatening to call the cops on him for being there, most people up here tipped well. While he didn’t like the way some of the residents looked at him, he at least begrudgingly understood. A 6’7” powerfully built, mahogany skinned gentleman such as himself was imposing. And it didn’t hurt that a lot of wives up here were willing to tip extra for some attention.

He walked up the stone stairs and along the cobblestone path, and waited patiently after he knocked. The door opened and he was stunned for a second. This little jailbait girl answered the door, with just some striped briefs and an open white button up on. The girls nonexistent tits exposed and her nipples looking like 2 tiny pink erasers. The girl had a booty though, her hips just stretched those panties.

“Daddy! Pizza is here! Where’s the money?” The cutesy song song voice got to Derrick, he had never thought of jailbait as all that tempting, but this one was. The kid had turned around and bent over slightly to call out in an exaggerated manner. Derrick thought “damn, that booty does not belong on someone so young.” At least, he believed he said that in his head.

“So you like my booty mister?” Jaime turned around and smiled impishly. The mixture of those green eyes, soft features and that perfect butt roused Derricks impressive cock. He normally had to hang down a pant leg, because underwear couldn’t really hold it. It stiffened and jerked, bulging out at his knee. “Oh, you really like it don’t you?” Jaime teased.

Just as Jaime began to reach out to touch it, Nathan came to the door, and told Jaime to put on clothing if he answers the door. “Boys his age are just nothing but energy, but no focus at all. Here’s a 100$, for your trouble. Hope he didn’t bother you too much. All right young man, let’s eats!” As the door closed, Derrick whispered to himself “he?”.

Derrick went back to his car, dumbfounded by this new revelation. His 16” cock was as hard as steel, he was going to have to take this out on one of the housewives nearby.

————————————-

Jaime and Nathan curled up on the couch and ate while watching a new superhero movie that Jaime had been wanting to see. “So what’s my present, daddy?” Jaime asked. Nathan smiled down at his little lover and said “something I thought would look good on you.” Jaime squealed and kicked his legs with excitement.

After dinner, Nathan told him that it was in the bathroom. Jaime bounced and skipped away, his booty jiggling the whole way. A few minutes later Jaime came back into the living room. Nathan was mesmerized.

Jaime walked in slowly, swaying his hips back and forth. His tiny nipples just barely visible under the stretchy white lace halter, the garter belt around his waist wasn’t to tight. The tiny penis poking out the top of the sheer g-string and the stockings attached to the garters, perfect. Jaime looked amazing, like a tiny bride on her wedding night, just like Nathan thought.

Nathan was completely naked when he came back, Jaime slowly walked up to his grown lover and gently kissed the leaking tip of his footlong, hard cock. Jaime locked up and down the mans shaft, kissing and slurping and licking up and down. “Aaaaaaaaah!” Jaime moaned with hot breath on Nathan’s stiff penis.

Slowly he climbed up on the strong, handsome man, swinging his legs over his stomach. Jaime sat back, Nathan’s cock between his plump cheeks and oozing onto his back. Jaime leaned in, holding Nathan’s face and kissed him. He whispered into the mans lips “i love it, do i look good?” Nathan kissed Jaime back. “You look amazing, but I think you already knew I liked it.”

“Fuck me daddy. Fuck me like you love me. Fuck me like you need me. Fuck me like I can get pregnant. Fuck me like I’m your wife.” Jaime whispered into Nathan’s ear as he stood up on the couch, pulling his g-string to one side. He grabbed the throbbing head, almost as big as his own fist, and positioned it under him. He sat down, and pushed down until Nathan’s cock was in him.

He moved up and down, slowly taking more and more. The giant dick stretching his hole like always, until he rested his fat bubble bottom on Nathan’s hips, thin cum dribbling from the boys penis. “yes daddy, nothing is as good as this”. Nathan twitches his cock, and the bulge in Jaimes tummy moved. He bucked up, the boy moaned.

Jaime started to grind into the man, with every few strokes, he would squirt a little more. He came about 5 times just from this, he was getting dizzy, his head just flashing pink every time Nathan thrusted. Jaime rode Nathan’s cock and slapped his soft, fat bottom down.

They did it slowly, they did it fast, neither one getting enough of each other’s obscene bodies. They kissed, moaned, grunted and came countless times that first night. His brain over loaded with pleasure, Jaime fell asleep on Nathan’s chest. His long cock still deep in the boy, Nathan looked down at the feather weight beauty on top of him. He smiled and fell asleep, excited to love Jaime tomorrow.

The next morning, Nathan stirred awake. He felt something hot and wet on his dick. Looking down, he saw his little boyfriend happily sucking away at the mans well endowed penis. “Shlurp! Hi daddy!” He continued to suck. “I want to go shopping today! Shlurp, gluk, gluk.” He took about two thirds of his dick down his hot tight throat. “ aaaahhh!” Jaime moaned as he pulled out and licked up the shaft.

“I think daddy should buy me some outfits for when we go out! Shhlup!” Back into Jaimes mouth went the large cock. How could a man say no? Nathan enjoyed the blowjob, finally cumming his first load down his throat. He then spent a few minutes licking at Jaimes tiny hole and boy clit. After that it was Balls deep until about ten thirty. “Let’s go out for breakfast, then we can go wherever you want to buy you some clothing just for us.” Nathan said with a laugh and a sigh.


End file.
